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Clinical data | |
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Other names | EBCO; Estradiol 3-benzoate 17β-cyclooctenyl ether |
Routes of administration | By mouth [1] |
Drug class | Estrogen; Estrogen ester; Estrogen ether |
Identifiers | |
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CAS Number | |
PubChem CID | |
ChemSpider | |
Chemical and physical data | |
Formula | C33H40O3 |
Molar mass | 484.680 g·mol−1 |
3D model ( JSmol) | |
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Estradiol benzoate cyclooctenyl ether (EBCO), or estradiol 3-benzoate 17β-cyclooctenyl ether, is a synthetic estrogen as well as estrogen ester and ether – specifically, the C3 benzoate ester and C17β cyclooctenyl ether of estradiol – which was described in the early 1970s and was never marketed. [1] [2] [3] [4] It has been found to have a dramatically prolonged duration of action with oral administration in animals, similarly to the related compound quinestrol (the 3-cyclopentyl ether of ethinylestradiol). [1] [5] [6] A single oral dose of EBCO sustained high uterus weights for 3 weeks in rats. [1] This long-lasting activity may be due to storage of EBCO in fat. [1] It appears that EBCO is absorbed satisfactorily from the gastrointestinal tract, at least partially survives first-pass metabolism in the liver and intestines, and is then sequestered into fat, from which it is slowly released and activated into estradiol. [1] In contrast to quinestrol, the oral activity of EBCO is greatly improved when it is delivered in an oil solution as opposed to an aqueous vehicle. [1]
![]() | |
Clinical data | |
---|---|
Other names | EBCO; Estradiol 3-benzoate 17β-cyclooctenyl ether |
Routes of administration | By mouth [1] |
Drug class | Estrogen; Estrogen ester; Estrogen ether |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
Chemical and physical data | |
Formula | C33H40O3 |
Molar mass | 484.680 g·mol−1 |
3D model ( JSmol) | |
| |
|
Estradiol benzoate cyclooctenyl ether (EBCO), or estradiol 3-benzoate 17β-cyclooctenyl ether, is a synthetic estrogen as well as estrogen ester and ether – specifically, the C3 benzoate ester and C17β cyclooctenyl ether of estradiol – which was described in the early 1970s and was never marketed. [1] [2] [3] [4] It has been found to have a dramatically prolonged duration of action with oral administration in animals, similarly to the related compound quinestrol (the 3-cyclopentyl ether of ethinylestradiol). [1] [5] [6] A single oral dose of EBCO sustained high uterus weights for 3 weeks in rats. [1] This long-lasting activity may be due to storage of EBCO in fat. [1] It appears that EBCO is absorbed satisfactorily from the gastrointestinal tract, at least partially survives first-pass metabolism in the liver and intestines, and is then sequestered into fat, from which it is slowly released and activated into estradiol. [1] In contrast to quinestrol, the oral activity of EBCO is greatly improved when it is delivered in an oil solution as opposed to an aqueous vehicle. [1]